Fukuzawa Shin-ichi, Yahara Yuusuke, Kamiyama Akira, Hara Masumi, Kikuchi Satoshi
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
Org Lett. 2005 Dec 22;7(26):5809-12. doi: 10.1021/ol0523291.
[reaction: see text] The pinacol coupling reaction of planar chiral ortho-oxazoline-substituted formylferrocene was smoothly mediated by SmI2 or Sm(OTf)3 to give the (R,R) isomer selectivity (up to 76% diastereomeric excess). The combination of Yb(OTf)3 and the (R,R)-ferrocenyl diol was revealed to be a good catalyst for the asymmetric Diels-Alder reaction of 3-acyloxazolidinone with cyclopentadiene, and the endo adduct was produced in up to 80% enantiomeric excess.
[反应：见正文] 平面手性邻恶唑啉取代甲酰基二茂铁的频哪醇偶联反应可通过SmI₂或Sm(OTf)₃顺利介导，得到（R,R）异构体选择性（非对映体过量高达76%）。结果表明，Yb(OTf)₃与（R,R）-二茂铁二醇的组合是3-酰基恶唑烷酮与环戊二烯不对称狄尔斯-阿尔德反应的良好催化剂，内型加合物的对映体过量高达80%。
